Microsoft President Brad Smith in his office in Redmond, Wash. (Uly Curry Photo)

As the tech industry’s unofficial diplomat to Washington, D.C., Microsoft President Brad Smith found himself in a bit of a bind.

Following Donald Trump’s election, political lines were being drawn in the sand with stark clarity. Polls overwhelmingly showed that people wanted companies to take stands and pick sides, including three quarters of workers aged 34 and below. In the tech sector, that meant the majority of employees.

Microsoft has a history of working with (and financially supporting) Republicans and Democrats in roughly equal measure, like many blue chip companies. But with the majority of millennials skewing further left, while Republicans gained control of Congress and the White House, Smith — labeled “a de facto ambassador for the technology industry at large” by The New York Times — needed a new way to walk the tightrope.

“This is a time when issues are harder to talk about,” Smith said during an interview in his Redmond, Wash., office, remarking on the country’s deepening partisanship. That presents a challenge, he said, given the increasing push for companies to “speak up” on hot button topics. “We didn’t address as many issues a decade ago as we do today.”

This is a time when issues are harder to talk about. We didn’t address as many issues a decade ago as we do today.

The morning after Election Day, Smith sensed a deep unease among Microsoft’s young employee base, and sat down to write a blog post reflecting on Trump’s win. The post struck a civil tone, sketching out Microsoft’s positions on issues including infrastructure and economic opportunity for people without college degrees — gesturing at themes from Trump’s campaign.

He also noted Microsoft’s four lawsuits against the Obama administration regarding law enforcement access to user data, to comfort those worried about Trump’s newfound powers over government surveillance infrastructure. One of those cases is set to be heard Feb. 27 at the U.S. Supreme Court.

Smith continued extending an olive branch to Trump voters as the inauguration came and went, arguing through a number of promoted LinkedIn blog posts that coastal city dwellers needn’t be the only beneficiaries of the tech economy. At the same time, he enlisted Microsoft in nearly every skirmish between the tech industry and the White House’s new occupants, on issues such as immigration and the Paris Agreement on climate change.

In both government and industry circles, Smith has a long reputation for taking the initiative on difficult subjects. This began in 2001, when Microsoft was in the midst of an ugly antitrust battle with the U.S. government. In his interview to become the company’s general counsel that year, Smith proposed that Microsoft start to consider a partial truce. He got the job, softened the company’s legal stance, and Microsoft avoided having its business broken into pieces by the feds.

Following the Edward Snowden revelations of 2013, Smith helped spearhead the industry’s response to consumer privacy concerns, coordinating with rivals like Google and Apple. This was a surprising about-face for Microsoft’s reputation in the tech world, which once regarded it as an intimidating brow-beater. Apple’s then-general counsel, Bruce Sewell, would later call Smith “good glue” for industry-wide initiatives.

Smith’s knack for bridging divides now faces a new test. He has made it clear that Microsoft has “good dialogue” with the Trump administration, and stands ready to partner with Trump and congressional Republicans on issues of common interest.

Nonetheless, if the tech elite has anything resembling a “resistance,” the publication Recode quickly labeled Smith its leader.

Mixing business and politics

Brad Smith brought a 30-year-old laptop to the House Judiciary Committee to illustrate the outdated nature of the Electronic Communications Privacy Act. (House Judiciary Committee Photo)

Partisan politics and business tend to mix like oil and water. People say they want companies to take stands, but polls also show 76 percent of consumers will stop supporting a business if that stand doesn’t suit their tastes. Everyone’s money is green, says the conventional business wisdom. Why scare off customers with controversial issues?

Nonetheless, Smith and his chief speechwriter Carol Ann Browne have been delving into a range of potentially touchy topics since last summer. Through written pieces, illustrations, and videos shot in locations around the world, the two have covered the increasing automation of jobs, government-sponsored cyber-warfare, international diplomacy, small business creation in the heartland, and more, using moments from history as jump-offs.

On the surface, the series — named “Today in Technology,” and distributed both through LinkedIn and a dedicated section of Microsoft’s site — seems to adhere to another business axiom: when the time comes to “engage” in the national conversation, it’s best to keep sentiments feel-good and indirect.

The tech sector is connected to so many critical issues, and yet if you just show up and say you want to talk about (an issue like) immigration, people have an opinion before you even open your mouth.

Smith was upfront about this. Customers and employees want to see Microsoft get involved on important topics, he said, and the series “gives us ability to combine a new approach, perhaps a softer approach, with the need to address more issues.”

But beyond the optimism of the stories Smith and Browne tell — heavy on messages of cooperation, empowerment, and a brighter future — there’s something ambitious about the fact they’re telling them, going well beyond most other executives in trying to make sense of the new age.

Take the entry on the Red Cross, for example. Smith and Browne go into detail on the group’s origins, and the international norms that allow them to operate on battlefields and in war zones. They use that story to argue specifically for a new “Digital Geneva Convention,” which would protect civilian infrastructure like water treatment facilities from state-sponsored cyber attacks.

“Like any analogy, the comparisons to the 19th century can be taken too far,” they write. “But the parallels nonetheless are noteworthy. Amidst increasing threats from a new generation of technological weapons, the world needs inspiration for a global conversation about the steps needed to protect people from these new dangers. The founding of the Red Cross provides a good start.”

Other times the message is a bit more inscrutable. In their most recent entry, Smith and Browne essentially host a short documentary on the “Walk in the Woods,” a famous incident in which the two chief negotiators for the U.S. and U.S.S.R. went for a private stroll during a 1982 nuclear summit, and attempted to work out concessions outside the hearing of their respective countries (fears of a wiretapped apartment spurred the walk itself).

The video alludes to some grim current affairs, such as nuclear tensions with North Korea. For an entry about preventing the end of human civilization, Browne said its message is pretty simple and inoffensive: “We’ve been here before. The feeling that these are unprecedented times, we’ve been here before, and there’s parallels you can draw.” Smith said it serves “to highlight the importance of diplomats and diplomacy.”

Read between the lines, though, and it could be saying something more subversive.

One takeaway from the “Walk in the Woods” is that diplomacy, unlike democracy, tends to thrive in darkness. It took private conversation, away from public scrutiny, to start thawing negotiations between two nuclear superpowers. It’s when decision-makers can keep their cards close to their vest, conversation frank, and options open, that big things have traditionally gotten done.

For an executive who admits to feeling pressure to publicly engage on issues, the entry could be seen as a rebuttal to the idea that taking open stands is necessarily superior to closed-door negotiations. It could also offer a glimpse at the series’ guiding principle, in which Smith wants to foster conversation between opposing sides, but believes laying out explicit positions can derail things.

“The tech sector is connected to so many critical issues, and yet if you just show up and say you want to talk about (an issue like) immigration, people have an opinion before you even open your mouth,” Smith said.

And in an era in which nuclear warfare is threatened via Twitter, visiting Switzerland to produce an ode to quiet, professional diplomacy could be read as a sly bit of sedition.

A passion project

Brad Smith and his chief speechwriter Carol Ann Browne in an interview in Smith’s Redmond office. The two work together on a series called “Today in Technology.” (Uly Curry Photo)

A 25-year Microsoft veteran, Smith has gained a gift for distilling the tech industry’s various business and legal issues. The skill contributed to his rise from Microsoft’s general counsel to its president, and his role as tech’s unofficial emissary to the halls of political power. As his official speechwriter and editor, Browne has picked up a proficiency for these issues as well, complemented by a voracious appetite for history books focused on the 20th century.

This has made “Today in Technology” series something of a natural outlet for its authors, and a passion project they pursue almost exclusively in their own spare time. Last Thanksgiving, Smith sat in the lobby of a New York City hotel working on an entry for hours, while others in his party caught the annual Macy’s Parade.

While on vacation in Paris with her family, Browne had to excuse herself to spend time at internet cafés to keep another entry’s publication on track.

Inspired in part by historic tidbits Browne would use to spice up Smith’s speeches, the series has since “become my hobby outside of working hours,” Smith said. It’s taken on a personal importance for its authors, a way to impose sanity on a world in which political and social precedents are being rapidly discarded.

It’s also gained some of the characteristics of a full-fledged multimedia operation. There is a video crew that sometimes now accompanies Smith on trips to shoot historic bits, two post-grad researchers from the University of Washington pulling together material, and public presentations for some of the entries. A representative for Microsoft estimates that more than 1 million people have read the series to date.

With its attempts to stay above the fray and its overriding optimism, one imagines the series won’t do much to assuage the feelings of Microsoft’s most angst-filled employees or customers. But Smith feels his office is delivering an important message, and one that’s pretty uncharacteristic for a tech executive: while the world may seem to be in uncharted territory, there’s nothing new under the sun.

Drew Atkins is a journalist and writer in Seattle, and the recipient of numerous national and regional awards. His work has also appeared in the New York Times, Seattle Times, The Oregonian, InvestigateWest, Crosscut, Seattle Magazine, and others. He can be found on Twitter at @ByDrewAtkins and contacted at drewatkins1@gmail.com.